Quinazolone containing phenyl-azo-pyridine compounds

ABSTRACT

Azo pigments of the formula:   IN WHICH R1 is hydrogen, chloro, bromo or nitro; R2 and R3 are water-insoluble and are hydrogen or chloro; R4 is hydrogen, chloro or methyl; and X is cyano or carbamoyl. The pigments are eminently suitable for coloring resins, surface coatings or printing inks.

Unite States Patent Dimroth 1 Dec. 2, 1975 I 1 QUINAZOLONE CONTAINING Primary ExaminerLorraine Ajweinberger PHENYL-AZO-PYRIDINE COMPOUNDS Assistant ExaminerC. F. Warren [75] Inventor Peter Dimmth Ludwigshafen Attorney, Agent, or Firm-Johnston, Keil, Thompson Germany & Shurtleff [73] Assignee: Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen [57] ABSTRACT (Rhine), Germany Azo pigments of the formula:

[22] Filed: Apr. 4, 1973 [21] Appl. No.: 348,083 [44] Published under the Trial Voluntary Protest R 0 R4 N=N X Program on January 28, 1975 as document no. 2 H I B 348,083. R HO N OH 30 Foreign Application Priority Data R Apr, 20, 1972 Germany 2219169 52 l. in which 1 U S C R is hydrogen, chloro, bromo or mtro; [51] Int C12 C09B 25/36 R and R are water-insoluble and are hydrogen or hlora l [58] Fle d of Search 260/154 R 15 hydrogen, chloro or methyl; and [56] References Cited X is cyano or carbamoyl. The pigments are 6/1964 United Kingdom 260/154 eminently suitable for coloring resins, surface coatings or printing inks.

4 Claims, N0 Drawings QUINAZOLONE CONTAINING PI-IENYL-AZO-PYRIDINE COMPOUNDS The invention relates to dyes of the formula (I):

R is hydrogen, chloro, bromo or nitro;

R is hydrogen or chloro;

R is hydrogen or chloro;

R is hydrogen, chloro or methyl; and

X is cyano or carbamoyl.

The new dyes have pigment properties and have very good solvent fastness properties in all solvents, migration fastness, overcoating fastness, overspraying fastness and good lightfastness. Very bright yellow to orange colorations are obtained.

Individual pigments of formula (I) have extremely high yield and depth of color or-in suitable physical form they have unusually good hiding power.

The new pigments are particularly suitable for the production of printing inks and for coloring for example plastics such as polyvinyl chloride or polystyrene, coating compositions or rubber.

Compounds in which R to R are all hydrogen are particularly important.

Compounds of the formula (I) may be prepared by reacting a diazo compound of an amine of the formula by a conventional method.

Amines of formula (II) are disclosed in Chem.Abst. 56, 8222:1(1962).

The physical form in which the pigments are ob-- tained in their preparation is often not the most favorable for the various applications but they can be converted into the most suitable form for the particular purpose by conditioning by a conventional method, for example by heating in water or an organic solvent in the presence or absence of additives or by conversion into appropriate formulations.

The following Examples illustrate the invention. Parts and percentages given in the Examples are by weight unless otherwise stated.

EXAMPLE 1 237 parts of 2-(4-aminophenyl)-quinazolone-4 is diazotized conventionally in sulfuric acid and the diazo solution is stirred into a mixture of 3,000 parts of water and 800 parts of ice. 150 parts of 2,4-dihydroxy-3- Cyano4-methylpyridine is then added followed by concentrated aqueous sodium acetate solution until a pH of from 5 to 6 has been set up. The whole is then stirred forfour hours, suction filtered and washed thoroughly with water. The moist filter cake obtained is stirred in 3,000 parts of glacial acetic acid at 120C for 5 hours in such a way that water can distil off. The product is suction-filtered, washed with water and dried. 340 parts of a yellowish orange powder is obtained in this way. It

has the formula:

CH I H @p@i1t CN H if H When 237 parts of 2-( 3-aminophenyl)-quinazolone-4 is used in the above method 348 parts of a yellow powder is obtained; the compound has the formula:

with a coupling component of the formula (III): 40 CIH I f, N=N I\ H N OH.

45 (III) I N Similar pigments are obtained with the amines set out in the following Table:

Parts Shade Amine of pigment 9 2 271 H 408 reddish yellow ,).C?c1 NH Cl 3 271 406 yellowish oran e (two modifications I NH O 271 410 greenish yellow -Continue'd Ex- Parts Parts Shade ample of Amine of pigamine ment 5 251 QCE 38o reddish yellow O.Z- 29, 9. 6 2 1 O CH 5 5 585 reddish yellow I! H CH3 7 285 590 yellow.

NH O 2 01 NH 8 305 410 yellow NH A 2 9 271 NH 410 yellow Cl N/ 3 When the compound of the formula: 3. Plastics 35 Flexible'polyvinyl chloride.

APPLICATION 1. Printing ink Varnish printing ink for letterpress and offset printing.

parts of the pigment of Example 1, paragraph 2, and 80 parts of a letterpress and offset varnish are ground (dispersed) on a three-roll mill. The printing ink thus obtained gives very bright yellow prints which have excellent fastness to overlacquering, good light fastness andgreat depth of shade.

2. Coating composition Surface coating based on alkyd-melamine resin for baking; full tone.

5 parts of the pigment of Example 1, paragraph 1. and 95 parts of a baking coating composition mixture of 70 percent of coconut-alkyd resin (based on coconut oil 60 percent in xylene) and percent of melamine resin solution (about 55 percent in butanol/xylene) are milled in an attritor mill. 100 parts of full tone coating composition is thus obtained. A coating prepared therewith is baked for about 30 minutes at 120C.

A bright orange coating is obtained which is distinguished by particularly good hiding power. excellent fastness to overspraying and good iightfastness.

0.1 part of the pigment from Example 1, paragraph 1, and 50 parts of a flexible PVC mixture of 65 parts of PVC powder, parts of a plasticizer based on phthalic acid and C to C alcohols and 2 parts of a stabilizer-are homogeneously dispersed on mixing rolls. A bright orange material is obtained in this way. The color has very good fastness to migration and light and particularly good hiding power. 7

Similar results are obtained when the pigment of Example l is replaced by pigments'specified in the other Examples.

We claim: l

1. A quinazolone azo pigment of the formula of R to R is hydrogen and X is cyano or carbamoyl.

3; Theazo pigment of the formula CH H Q EN 4. The azo pigment of the formula UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,923,774 0 DATED December 2, 1975 INVENTOR(S) DIMROTH It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

In the Abstract, Line 4, delete R and R are waterinsoluble and are hydrogen or chloro;" and substitute --R and R are hydrogen or chloro;--

O In the Abstract, Line 7, after the word "are" insert --water-ins01uble and are-- In Column 3, Line 46, delete "1. Printing ink" and substitute --l. Printing ink:---

In Column 3, Line 54, delete "2. Coating composition" and substitute --2., Coating composition:--

In Column 4, Line 34, delete "Plastics" and substitute --Plastics:

Signed and Scaled this Twenty-first D y f September 1976 [SEAL] Q Arrest:

RUTH c. MASON c. MARSHALL DANN Arresting Officer I Commissioner uflfarenls and Trademarks 

1. A QUINAZOLONE AZO PIGMENT OF THE FORMULA
 2. An azo pigment as claimed in claim 1 where each of R1 to R4 is hydrogen and X is cyano or carbamoyl.
 3. The azo pigment of the formula
 4. The azo pigment of the formula 